


Fortune Favors the Bold

by BeccaAnne814



Series: Steve Rogers x Reader Oneshots [6]
Category: Captain America (Movies), Captain America - All Media Types, Marvel, Marvel Cinematic Universe, The Avengers (Marvel Movies), The Avengers (Marvel) - All Media Types
Genre: F/M, Fluff, Probably a curse word or two
Language: English
Status: Completed
Published: 2020-01-20
Updated: 2020-01-20
Packaged: 2021-02-26 08:14:49
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22334227
Author URL: https://archiveofourown.org/users/BeccaAnne814/pseuds/BeccaAnne814
Summary: Steve sees a man wearing a coat with a controversial statement written across the back.  Realizing that he’s in a position to do something about it, he has to work up his nerve to get past Pepper’s extremely attractive—and flirtatious—admin to pitch his idea.
Relationships: Steve Rogers x Reader
Series: Steve Rogers x Reader Oneshots [6]
Series URL: https://archiveofourown.org/series/772464
Comments: 4
Kudos: 30





	Fortune Favors the Bold

**Steve Rogers x Reader**

**Summary** – Steve sees a man wearing a coat with a controversial statement written across the back. Realizing that he’s in a position to do something about it, he has to work up his nerve to get past Pepper’s extremely attractive—and flirtatious—admin to pitch his idea. 

**Warnings** – Fluff…probably a curse word or two

**Word Count** – 1K

**Notes:** At the end.

_ ** [Masterlist](https://beccaanne814.tumblr.com/post/174989754188/masterlist) ** _

[[MORE]]

"Don't give money to the Arts," Steve muttered under his breath as he read the back of the man's jacket in front of him in the coffee cart queue.

The man wearing the jacket turned around and gave Steve a grin. "Pisses you off, doesn't it?"

Steve's eyebrows drew together in his signature look of disapproval. "Well, now that you mention it—it sorta does."

The man nodded. "That's the point." When Steve's face morphed into one of pure confusion, the man continued. "It's simple reverse psychology. If you ask people to donate to the Arts, they hem and haw, and complain that there are other causes that deserve more attention. But the second you thumb your nose at something, everyone gets all riled up and jumps on the bandwagon."

Steve thought about his own reaction to the message on the coat and realized the man was right. As he waited in line to buy his morning coffee, he tried to figure out a way that he could somehow help to promote funding of the Arts. When he'd been a sickly kid in Brooklyn before the war, his sketchbook and pencils had been the only outlet he'd had for his pent up frustrations. He'd since traded his drawings for beating up Nazi's, but every now and then he'd find himself sketching out something during a mission briefing.

Making his way back to the Tower, he walked into the lobby and nodded toward the security guard behind the front desk. The old man was well past the age of retirement, but with his bushy white mustache and tinted glasses, he'd become a fixture in the Avengers' Tower.

Steve had never paid much attention to the directory that hung behind the desk, but as his gaze flitted over the security guard, one of the corporations on the board caught his eye.

The September Foundation.

Tony and Pepper had created the group to help fund the students at MIT, but he was sure if he pitched his idea to Pepper, she'd see the benefit of funding the Arts as well. The only problem would be getting past her admin.

It wasn't that YN had an intimidating personality—she just intimidated the hell out of him. With her easy smile and laughing eyes, she could make him feel like a love-sick schoolboy with just one look.

His mind was telling him to just forget the whole thing, but his heart must have had other plans as he found himself pressing the elevator button for the September Foundation's floor. Steeling his nerves, he gave himself a mental pep talk about playing it cool and keeping his interaction with YN purely professional.

"Captain Rogers," YN all but purred as she watched the handsome blond step off the elevator. "What can I help you with today?"

"I need to see Pepper if she's in," Steve said evenly, proud of himself for not blushing as YN gazed up at him with a bright smile.

YN shook her head sadly. "She's not, but I can take a message for her."

He almost told her to never mind, but he knew this idea would gnaw at him all day until he'd at least tried to get Pepper on board. As quickly as he could, he explained the incident in by the coffee cart to YN, and thankfully, she didn't interrupt as he laid out his idea for a new division of the September Foundation that would help fund Art programs for underprivileged children.

"I think that's a great idea," YN said once he'd finished.

"But will Pepper and Tony?"

YN brushed aside his concern. "Tony does whatever Pepper tells him to do, and. . ." She paused and gave him a little smirk. ". . .Pepper is easily persuaded if you know how what buttons to push."

Steve already knew the answer to his question, but he asked anyway. "I take it you know what buttons to push?"

YN nodded. "And I might be willing to help you out. . ."

She let her sentence trail off and Steve felt his stomach drop. Swallowing hard, his heart began to race. "What will it cost me?"

Leaning forward on her desk, she rested her chin on her interlaced fingers and adopted a purely innocent look. "Not much—just a cup of coffee."

Instinctively Steve held out the fresh cup he'd yet to take a sip of since buying it downstairs. "Here, have this one."

Trying and failing to contain her laughter, YN sat back and slowly shook her head. Sighing, she realized that she was going to have to spell it out for him. "I meant that you and I would actually go to the coffee shop together. You know, like a date?"

The perpetual blush Steve normally sported when he was around her began creeping up his neck and setting his whole face on fire. She'd just asked him out, and he couldn't think of a single reason why he should say no. It did go against all of his ideas of proper dating etiquette for her to be the one to ask him out, but it was the twenty-first century, and it wasn't like he was going to work up the nerve to ask her out before the next one rolled around anyway.

He looked down at the cup in his hand and then back up at her with a shy smile. "This one's probably cold—want to go get another one with me right now?"

Hitting the button to send incoming calls to voicemail, YN grabbed her jacket and walked around the desk with a smile. Steve was waiting with his arm outstretched, so she looped hers through his and tried to will her feet to stay rooted to the ground. She'd never dreamed her boldness would get past his bashfulness, but she was glad she'd made the first move. Pepper would be thrilled with the idea to fund an Arts program, and YN vowed to be the first person to make a donation—it was only fitting, after all.

______________________

_Author's Note: Thank you for reading Day 259 of my writing challenge. I hope you enjoyed it! This prompt was created with Steve Rogers in mind, don’t you agree? I love writing shy, smitten Steve paired with a bold and sassy Reader. As an Art teacher, this prompt hit really close to home, and I’d love to have an organization like the September Foundation help fund all the schools in my home state. But I guess I’ll just have to keep dreaming and writing about it because it’s probably never going to happen. . . Anyway, I look forward to your comments, and if you enjoyed this story, please consider reblogging!_


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